反应详情

温度

80 °C

To a solution of 4-aminophenol (0.87 g, 8.0 mmol) in DMSO (12 mL) was added cesium carbonate (3.1 g, 9.6 mmol) and 2-fluoro-3-picoline (0.89 g, 8.0 mmol). The resulting mixture was heated to 80° C. for 16 h. After cooling to RT, the reaction mixture was diluted with EtOAc and washed with water and brine several times to remove DMSO. The aqueous layer was back extracted with EtOAc and the combined organic layer was dried (Na2SO4) and concentrated. The crude product was chromatographed through a RediSep® pre-packed silica gel column (120 g), eluting with a gradient of 0% to 30% EtOAc in hexane, to provide 4-(3-methylpyridin-2-yloxy)benzenamine as tan solid. MS (ESI, pos. ion) m/z: 201.2 (M+1).

1. temperatureAfter cooling to RT
2. washwashed with water and brine several times
3. customto remove DMSO
4. extractionThe aqueous layer was back extracted with EtOAc
5. dry with materialthe combined organic layer was dried (Na2SO4)
6. concentrationconcentrated
7. customThe crude product was chromatographed through a RediSep® pre-packed silica gel column (120 g)
8. washeluting with a gradient of 0% to 30% EtOAc in hexane